(+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate

Base Information

• Chemical Name: (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate
• CAS No.: 904916-30-9
• Molecular Formula: C₂₉H₂₆Cl₂N₂O₄S₂
• Molecular Weight: 601.574
• Mol file: 904916-30-9.mol

Synonyms:(+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate

Chemical Property of (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate

There total 10 articles about (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-(2-Amino-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-ethylsulfanyl)-propionic acid methyl ester + 4-chlorobenzenesulfonyl chloride (98-60-2) → (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate (904916-30-9)

Guidance literature:

With triethylamine; In 1,2-dichloro-ethane; at 5 ℃; for 12h;

DOI:10.1248/cpb.54.603

Reference yield:

methyl 3-[(E)-2-(7-chloro-2-quinolyl)vinyl]benzoate (203940-17-4) → (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate (904916-30-9)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. NaOH / tetrahydrofuran; methanol / 3 h / 40 °C

2: 93 percent / K₂CO₃*1.5H₂O; diphenylphosphoryl azide / dimethylformamide / 20 h / 20 °C

3: 98 percent / aq. HCl / ethanol / 6 h / Heating

4: 55 percent / sodium borohydride; potassium carbonate / ethanol / 1 h / 20 °C

5: 18.8 g / toluene / 3 h / 160 °C / 3 Torr

6: 19.0 g / pyridine / 1,2-dichloro-ethane / 12 h / 20 °C

7: 15 percent / cesium carbonate / dimethylsulfoxide / 1 h / 20 °C

8: methylhydrazine / ethanol; dioxane / 7 h / Heating

9: triethylamine / 1,2-dichloro-ethane / 12 h / 5 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; diphenylphosphoranyl azide; potassium carbonate; caesium carbonate; triethylamine; methylhydrazine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.54.603

Reference yield:

(+/-)-2-amino-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethanol (203940-21-0) → (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate (904916-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 18.8 g / toluene / 3 h / 160 °C / 3 Torr

2: 19.0 g / pyridine / 1,2-dichloro-ethane / 12 h / 20 °C

3: 15 percent / cesium carbonate / dimethylsulfoxide / 1 h / 20 °C

4: methylhydrazine / ethanol; dioxane / 7 h / Heating

5: triethylamine / 1,2-dichloro-ethane / 12 h / 5 °C

With pyridine; caesium carbonate; triethylamine; methylhydrazine; In 1,4-dioxane; ethanol; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene;

DOI:10.1248/cpb.54.603

upstream raw materials:

4-chlorobenzenesulfonyl chloride

methyl 3-[(E)-2-(7-chloro-2-quinolyl)vinyl]benzoate

(+/-)-2-amino-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethanol

ethyl 5-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}oxazol-4-carboxylate